Synthesis, Characterization, and Biological Activity of a New Class of Dialkylphosphorylhydrazone Derivatives of Isatin

Zampirolli, Letícia Silotti; Lemos, Marcela Jacques de; Goncalves, V.; Souza, Marco Andre Alves de; Souza, Sônia Regina de; Rumjanek, Víctor Marcos; DaCosta, João Batista Neves

doi:10.5935/0100-4042.20140162

Cited by 4 publications

(4 citation statements)

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“…Evaluation of the fungicidal activity of dialkylphosphorylhydrazones showed that several compounds are able to effectively inhibit the growth of Rhizoctonia solani and Fusarium oxysporum. In addition, these compounds did not interfere with the germination of lettuce seeds, which indicates the absence of phytotoxicity and makes them potential leaders in the search for new fungicides [39].…”

Section: Introductionmentioning

confidence: 93%

Anticancer and Antiphytopathogenic Activity of Fluorinated Isatins and Their Water-Soluble Hydrazone Derivatives

Bogdanov,

Neganova,

Voloshina

et al. 2023

IJMS

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A series of new fluorinated 1-benzylisatins was synthesized in high yields via a simple one-pot procedure in order to explore the possible effect of ortho-fluoro (3a), chloro (3b), or bis-fluoro (3d) substitution on the biological activity of this pharmacophore. Furthermore, the new isatins could be converted into water-soluble isatin-3-hydrazones using their acid-catalyzed reaction with Girard’s reagent P and its dimethyl analog. The cytotoxic action of these substances is associated with the induction of apoptosis caused by mitochondrial membrane dissipation and stimulated reactive oxygen species production in tumor cells. In addition, compounds 3a and 3b exhibit platelet antiaggregation activity at the level of acetylsalicylic acid, and the whole series of fluorine-containing isatins does not adversely affect the hemostasis system as a whole. Among the new water-soluble pyridinium isatin-3-acylhydrazones, compounds 7c and 5c,e exhibit the highest antagonistic effect against phytopathogens of bacterial and fungal origin and can be considered useful leads for combating plant diseases.

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Section: Introductionmentioning

confidence: 93%

Anticancer and Antiphytopathogenic Activity of Fluorinated Isatins and Their Water-Soluble Hydrazone Derivatives

Bogdanov,

Neganova,

Voloshina

et al. 2023

IJMS

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“…Due to the mixture of diastereoisomer obtained, duplications of the results in the presented spectra were observed. The ratio of the diastereoisomers is described in Table 9 , which is preferred for the diastereoisomer E due to the prior works [1] , [2] , [3] , [4] , [5] , [6] , [7] ( Fig. 1 , Fig.…”

Section: Datamentioning

confidence: 99%

Synthesis and characterization of new dialkylacylphosphonylhydrazones

et al. 2018

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The present work refers to the synthesis of novel dialkylacylphosphonylhydrazones that occurs in three reaction steps: the first one is the synthesis of different dialkyl acetate phosphonoacetates obtained by the reaction of ethyl bromoacetate with the trialkyl phosphite of interest. The second one is the synthesis of acetic diethoxyphosphonylhydrazines which is from the reaction between the synthesized dialkyl phosphonoacetates and hydrazine. The third and final steps is the condensation of acetic diethoxyphosphonylhydrazides with different heterocyclic aldehydes. In total, 17 unpublished compounds, namely 1 to 17 (Table 1) were obtained with a diastereoisomeric mixture of the preferential conformation E and all the compounds were characterized by 1-H and 13-C and 31-P NMR, infrared (IR) and mass spectroscopy (MS). This work presents the characterization data of these compounds.

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“…The progressing number of works on synthetic procedures [3] and the studies of this heterocycle push researchers in this area to publish generalized data on one or another type of biological activity [4][5][6][7]. It is due to the manifestation of isatin and its derivatives of a wide spectrum of activity, such as anti-cancer [8][9][10], anti-tubercular [11,12], antibacterial [13], anti-COVID [14,15], fungicidal [16,17], etc (Fig. 1).…”

Section: Introductionmentioning

confidence: 99%

Synthesis and diverse biological activity profile of triethylammonium isatin-3-hydrazones

Богданов¹,

Tsivileva²,

Voloshina³

et al. 2022

ADMET DMPK

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A series of biorelevant triethylammonium isatin hydrazones containing various substituents in the aromatic fragment have been synthesized. Their structure and composition were confirmed by NMR- and IR-spectroscopies, mass-spectrometry and elemental analysis. It was found that some representatives show activity against Staphylococcus aureus and Bacillus cereus higher or at the level of norfloxacin, including methicillin-resistant Staphylococcus aureus strains. The study also showed low hemo- and cytotoxicity (Chang Liver) and high antiaggregatory and anticoagulant activity of these compounds. The high potential of new ammonium isatin-3-acylhydrazones in the search for antimicrobial activity against phytopathogens of bacterial and fungal nature has been shown for the first time.

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Synthesis, Characterization, and Biological Activity of a New Class of Dialkylphosphorylhydrazone Derivatives of Isatin

Cited by 4 publications

References 0 publications

Anticancer and Antiphytopathogenic Activity of Fluorinated Isatins and Their Water-Soluble Hydrazone Derivatives

Anticancer and Antiphytopathogenic Activity of Fluorinated Isatins and Their Water-Soluble Hydrazone Derivatives

Synthesis and characterization of new dialkylacylphosphonylhydrazones

Synthesis and diverse biological activity profile of triethylammonium isatin-3-hydrazones

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